EP1219633A4 - Procede de production d'un derive d'aspartame, cristaux de ce derive, production de nouveaux intermediaires associes et procede de production de l'intermediaire - Google Patents

Procede de production d'un derive d'aspartame, cristaux de ce derive, production de nouveaux intermediaires associes et procede de production de l'intermediaire

Info

Publication number
EP1219633A4
EP1219633A4 EP00964672A EP00964672A EP1219633A4 EP 1219633 A4 EP1219633 A4 EP 1219633A4 EP 00964672 A EP00964672 A EP 00964672A EP 00964672 A EP00964672 A EP 00964672A EP 1219633 A4 EP1219633 A4 EP 1219633A4
Authority
EP
European Patent Office
Prior art keywords
producing
methoxyphenyl
crystals
hydroxy
novel production
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP00964672A
Other languages
German (de)
English (en)
Other versions
EP1219633A1 (fr
Inventor
Shigeru Kawahara
Kazutaka Nagashima
Kenichi Mori
Tadashi Takemoto
Eriko Ono
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ajinomoto Co Inc
Original Assignee
Ajinomoto Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ajinomoto Co Inc filed Critical Ajinomoto Co Inc
Publication of EP1219633A1 publication Critical patent/EP1219633A1/fr
Publication of EP1219633A4 publication Critical patent/EP1219633A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid
    • C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
    • C07K5/0613—Aspartame
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
    • A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Peptides Or Proteins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Seasonings (AREA)

Abstract

On produit du 3-(3-hydroxy-4-méthoxyphényl)-3-méthylbutyl aldéhyde au moyen d'une réaction dans laquelle on convertit en groupe formyle, le groupe carboxyle de l'acide 3-(3-hydroxy-4-méthoxyphényl)-3-méthylbutryrique, qui peut être obtenu au moyen de la réaction d'un 2-halogénoanisole avec du 3-acide méthylcrotonique et de la conversion en un groupe hydroxyle, de l'atome halogène de l'acide 3-(3-halogéno-4-méthoxyphényl)-3-méthylbutyrique ainsi produit. Par une réaction d'alkylation réductrice avec l'aspartame, ce dérivé aldéhyde peut être facilement et efficacement transformé à l'échelle industrielle en N-[N-[3-(3-hydroxy-4-méthoxyphényl)-3-méthylbutyl]-L-α-aspartyl]-L-phénylalanine 1-méthyl ester qui est utile en tant qu'édulcorant ayant un goût sucré très puissant. Ce dérivé aldéhyde est par conséquent extrêmement utile en tant qu'intermédiaire dans la production de l'édulcorant.
EP00964672A 1999-10-08 2000-10-04 Procede de production d'un derive d'aspartame, cristaux de ce derive, production de nouveaux intermediaires associes et procede de production de l'intermediaire Withdrawn EP1219633A4 (fr)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
JP28820899 1999-10-08
JP28820799 1999-10-08
JP28820799 1999-10-08
JP28820899 1999-10-08
JP29440999 1999-10-15
JP29440999 1999-10-15
JP32809999 1999-11-18
JP32809999 1999-11-18
PCT/JP2000/006933 WO2001027142A1 (fr) 1999-10-08 2000-10-04 Procede de production d'un derive d'aspartame, cristaux de ce derive, production de nouveaux intermediaires associes et procede de production de l'intermediaire

Publications (2)

Publication Number Publication Date
EP1219633A1 EP1219633A1 (fr) 2002-07-03
EP1219633A4 true EP1219633A4 (fr) 2004-10-20

Family

ID=27479481

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00964672A Withdrawn EP1219633A4 (fr) 1999-10-08 2000-10-04 Procede de production d'un derive d'aspartame, cristaux de ce derive, production de nouveaux intermediaires associes et procede de production de l'intermediaire

Country Status (8)

Country Link
US (2) US20020132032A1 (fr)
EP (1) EP1219633A4 (fr)
KR (1) KR20020038797A (fr)
CN (2) CN1378556A (fr)
AU (1) AU7556700A (fr)
BR (1) BR0014565A (fr)
CA (1) CA2386859A1 (fr)
WO (1) WO2001027142A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20020038797A (ko) * 1999-10-08 2002-05-23 에가시라 구니오 아스파탐 유도체의 제조방법, 이의 결정, 이를 위한신규한 제조 중간체 및 당해 중간체의 제조방법
JP2001199930A (ja) * 2000-01-20 2001-07-24 Ajinomoto Co Inc 新規アリ−ルプロピルアルデヒド誘導体、その製造法及びその使用等
EP2433922A1 (fr) 2010-08-25 2012-03-28 Syngenta Participations AG Procédé pour la préparation dichlorofulvène
WO2017131138A1 (fr) * 2016-01-29 2017-08-03 シチズン時計株式会社 Liquide d'inspection destiné à une inspection pour distinguer un cuir traité par un composé de réduction de chrome hexavalent d'un autre
CN116284174A (zh) * 2023-03-07 2023-06-23 昆山亚香香料股份有限公司 一种电子烟甜味剂及生产工艺及应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5510508A (en) * 1994-05-09 1996-04-23 Claude; Nofre Method of preparing a compound derived from aspartame, useful as a sweetening agent
WO1998032767A1 (fr) * 1997-01-29 1998-07-30 The Nutrasweet Company Procede destine a la preparation et a la purification d'un derive d'aspartame n-alkyle
EP1114828A1 (fr) * 1998-09-18 2001-07-11 Ajinomoto Co., Inc. Derives d'ester n-alkylaspartyldipeptidique et edulcorants

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60193940A (ja) * 1984-03-16 1985-10-02 Mitsui Toatsu Chem Inc 新規芳香族アルケン化合物
FR2697844B1 (fr) * 1992-11-12 1995-01-27 Claude Nofre Nouveaux composés dérivés de dipeptides ou d'analogues dipeptidiques utiles comme agents édulcorants, leur procédé de préparation.
WO1999052937A1 (fr) * 1998-04-09 1999-10-21 Ajinomoto Co., Inc. Derives d'ester aspartyl dipeptidique et agents edulcorants
EP1088829A4 (fr) * 1998-06-26 2005-02-02 Ajinomoto Kk Nouveaux derives d'aspartyl dipetpide ester et edulcorants
AU6727300A (en) * 1999-09-07 2001-04-10 Ajinomoto Co., Inc. Process for producing aspartame derivative, method of purifying the same, crystals thereof and use of the same
US20040176472A1 (en) * 1999-10-07 2004-09-09 Ajinomoto Co., Inc. Process for production of aspartyl dipeptide ester derivative, novel production intermediate therefor, and process for production thereof
KR20020038797A (ko) * 1999-10-08 2002-05-23 에가시라 구니오 아스파탐 유도체의 제조방법, 이의 결정, 이를 위한신규한 제조 중간체 및 당해 중간체의 제조방법
CN1391553A (zh) * 1999-11-18 2003-01-15 味之素株式会社 高甜度甜味剂用的新型中间体以及它的制造方法
WO2001085761A1 (fr) * 2000-05-10 2001-11-15 Ajinomoto Co., Inc. Procede permettant de produire des derives d'aspartyle dipeptide ester

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5510508A (en) * 1994-05-09 1996-04-23 Claude; Nofre Method of preparing a compound derived from aspartame, useful as a sweetening agent
WO1998032767A1 (fr) * 1997-01-29 1998-07-30 The Nutrasweet Company Procede destine a la preparation et a la purification d'un derive d'aspartame n-alkyle
EP1114828A1 (fr) * 1998-09-18 2001-07-11 Ajinomoto Co., Inc. Derives d'ester n-alkylaspartyldipeptidique et edulcorants

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
BROUWER, D.M. ET AL.: "Cycliacylation of 3-phenylpropanoic and 4-phenylbutanoic acids in liquid hydrogen fluoride: kinetics, mechanism and substituent effects", RECL. TRAV. CHIM. PAYS-BAS, vol. 93, 1974, pages 189 - 194, XP009035419 *
NAGAYAMA K ET AL: "DIRECT HYDROGENATION OF CARBOXYLIC ACIDS TO CORRESPONDING ALDEHYDESCATALYZED BY PALLADIUM COMPLEXES IN THE PRESENCE OF PIVALIC ANHYDRIDE", CHEMISTRY LETTERS, CHEMICAL SOCIETY OF JAPAN. TOKYO, JP, no. 11, 1998, pages 1143 - 1144, XP000999904, ISSN: 0366-7022 *
RUECHARDT C ET AL: "Radikalumlagerungen. IV. WEITERE RELATIVE WANDERUNGSGESCHWINDIGKEITEN SUBSTITUIERTER PHENYLRESTE BEI DER DECARBONYLIERUNG VON BETA-ARYL-ISOVALERALDEHYDEN", CHEMISCHE BERICHTE, vol. 95, 1962, pages 1921 - 1942, XP009030916, ISSN: 0960-7722 *
SAWYER, J.S. ET AL.: "Total synthesis of (+/-)-N-acetylcolchinol", TETRAHEDRON LETTERS, vol. 29, no. 38, 1988, pages 4839 - 4842, XP002293337 *
See also references of WO0127142A1 *
WELLER, D.D. ET AL.: "Preparation of oxygenated phenylacetic acids", J. ORG. CHEM., vol. 49, no. 11, 1984, pages 2061 - 2063, XP002293338 *

Also Published As

Publication number Publication date
CA2386859A1 (fr) 2001-04-19
US20040230073A1 (en) 2004-11-18
KR20020038797A (ko) 2002-05-23
US20020132032A1 (en) 2002-09-19
AU7556700A (en) 2001-04-23
EP1219633A1 (fr) 2002-07-03
BR0014565A (pt) 2002-11-19
WO2001027142A1 (fr) 2001-04-19
CN1566141A (zh) 2005-01-19
CN1378556A (zh) 2002-11-06

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